3-(2-cyanovinyl)carbazole | 1044273-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(2-cyanovinyl)carbazole
• 英文别名: 3-Cyanovinylcarbazole；3-(9H-carbazol-3-yl)prop-2-enenitrile
• CAS: 1044273-21-3
• 化学式: C₁₅H₁₀N₂
• 分子量: 218.258
• InChiKey: HDAVJPSXEPLOMF-UHFFFAOYSA-N

物化性质

• 沸点：
  483.3±20.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-cyanovinyl)carbazole 在 吡啶 、 4-二甲氨基吡啶 、 水 、 sodium hydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 43.5h， 生成
  参考文献：
  名称：

  DNA Photo-Cross-Linking Using 3-Cyanovinylcarbazole Modified Oligonucleotide with Threoninol Linker

  摘要：

  3-Cyanovinylcarbazole modified d-threoninol (D-CNV) was incorporated in oligodeoxyribonucleotide and tested for a photo-cross-linking reaction with complementary oligodeoxyribonucleotide. The photoreactivity was 1.8- to 8-fold greater than that of 3-cyanovinylcarbazole modified deoxyribose (K-CNV) previously reported. From the results of melting analysis and circular dichroism spectroscopy of the duplexes, the relatively flexible structure of D-CNV compared with K-CNV might be advantageous for [2 + 2] photocycloaddition between the cyanovinyl group on the D-CNV and pyrimidine base in the complementary strand.

  DOI：

  10.1021/acs.orglett.5b00035
• 作为产物：
  描述：

  咔唑 在 sodium periodate 、 硫酸 、 碘 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 3-(2-cyanovinyl)carbazole
  参考文献：
  名称：

  METHOD OF SUPPRESSING FORMATION OF PHOTOCROSSLINK, AND PHOTOREACTIVE NUCLEIC ACID IN WHICH AUTO-CROSSLINK FORMATION IS SUPPRESSED

  摘要：

  提供了一种防止光响应核酸探针失活的方法，通过在可光交联的含有可光交联乙烯结构的光响应碱基和可光交联胸腺嘧啶（T）或尿嘧啶（U）碱基之间抑制光交联物的形成，通过用R基（R为—CN或—CO—R1，其中R1为饱和或不饱和直链或支链环状或非环状C1-12碳氢化合物基团）替代胸腺嘧啶（T）或尿嘧啶（U）碱基的嘧啶环的5位。

  公开号：

  US20160326207A1

文献信息

• PHOTORESPONSIVE NUCLEOTIDE ANALOGUE HAVING PHOTOCROSSLINKING ABILITY
  申请人：JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US20160031918A1

  公开（公告）日：2016-02-04

  The present invention provides a new photoreactive compound which can be used in technologies for photoreactions of nucleic acid, and also provides a photoreactive crosslinking agent comprising the above photoreactive compound. A photoreactive compound represented by the following formula I can be used.

  本发明提供了一种新的光反应化合物，可用于核酸的光反应技术，并提供了包括上述光反应化合物的光交联剂。可以使用以下式I表示的光反应化合物。
• LIGHT-RESPONSIVE ARTIFICIAL NUCLEOTIDE HAVING PHOTO-CROSSLINKING ABILITY
  申请人：Fujimoto Kenzo

  公开号：US20100274000A1

  公开（公告）日：2010-10-28

  The present invention provides a photoreactive crosslinking agent that is capable of crosslinking a sequence which cannot be photo-crosslinked by psoralen, and is capable of photo-crosslinking using a light having a longer wavelength, as compared with psoralen. The present invention also provides a compound having a group represented by formula (I) coupled with a group represented by formula (II).

  本发明提供了一种光反应性交联剂，该交联剂能够交联一种不能被光毒素交联的序列，并且能够使用比光毒素更长波长的光进行光交联。本发明还提供了一种化合物，该化合物具有由式（I）表示的基团与由式（II）表示的基团耦合的特征。
• Light-responsive artificial nucleotide having photo-crosslinking ability
  申请人：Fujimoto Kenzo

  公开号：US08481714B2

  公开（公告）日：2013-07-09

  The present invention provides a photoreactive crosslinking agent that is capable of crosslinking a sequence which cannot be photo-crosslinked by psoralen, and is capable of photo-crosslinking using a light having a longer wavelength, as compared with psoralen. The present invention also provides a compound having a group represented by formula (I) coupled with a group represented by formula (II).

  本发明提供一种光敏交联剂，能够交联无法被芳香植物酮光交联的序列，并且能够使用比芳香植物酮更长波长的光进行光交联。本发明还提供一种具有由式(I)表示的基团与由式(II)表示的基团偶联的化合物。
• Ultrafast Reversible Photo-Cross-Linking Reaction: Toward in Situ DNA Manipulation
  作者：Yoshinaga Yoshimura、Kenzo Fujimoto

  DOI：10.1021/ol801112j

  日期：2008.8.7

  We describe a novel ultrafast reversible DNA interstrand photo-cross-linking reaction via 3-cyanovinylcarbazole nucleoside ((CNV)K). Oligodeoxynucleotide (ODN) containing (CNV)K can be photo-cross-linked by irradiation at 366 nm for 1s, and the photo-cross-linked ODN can be split by irradiation at 312 nm for 60 s.
• Efficient synthesis of 3-cyanovinylcarbazole-1′-β-deoxyriboside-5′-triphosphate: a reversible photo-cross-linking probe
  作者：Anilkumar R. Kore、Balasubramanian Srinivasan

  DOI：10.1016/j.tetlet.2012.05.114

  日期：2012.8

  We describe an efficient synthesis of 3-cyanovinylcarbazole-1'-beta-deoxyriboside-5'-triphosphate containing light-responsive artificial nucleobase 3-cyanovinylcarbazole, which can be used as a reversible photo-cross-linking probe with nucleic acid compounds for various biological applications. A three-step synthesis of 3-cyanovinylcarbazole-1'-beta-deoxyriboside starting from 3-cyanovinylcarbazole, followed by 'one-pot, three-step' procedure is presented to accomplish the title compound 3-cyanovinylcarbazole-1'-beta-deoxyriboside-5'-triphosphate in good yields. (C) 2012 Elsevier Ltd. All rights reserved.